Actual Itinerary

This reflects what I actually did, not what I had planned. Originally, for example, I had planned on doing Scuba the first 2 days, but due to occupancy they had to move me back a day, which meant I couldn’t do the road to hana on the day I had signed up for the black sand beach.

Day 1: Sunday 5/28 - Arrival

• 3:30 PM - Arrive at OGG
• 4:00 PM - pickup rental car from Sixt
• Check in to hotel at Kihei
• Walk along coastline and enjoy sunset at Sunset Beach

Thoughts

• Probably should have tried to get a reservation at a fancy restaurant ahead of time, and then had a nice dinner somewhere.
• Alternatively, I could’ve avoided the day in Kihei entirely, and just gone directly to Lahaina. Probably would’ve been a slightly better use of time.

Day 2: Monday 5/29 - Haleakala

• 8:00 AM - check out of hotel
• 8:30 AM - 9:30 AM - drive to Lahaina along southwest coast
• 9:30 AM - 10:15 AM - jet ski!
• 11:00 AM - 12:30 PM - Maui Chocolate Tour
• 2:30 PM - 5:00 PM - drive to Haleakala summit
• 5:00 PM - 8:00 PM - hike around Haleakala summit trails nap
• 8:00 PM - 8:30 PM - watch the sunset
• 8:30 PM - 9:30 PM - astrophotography at summit
• 9:30 PM - 11:30 PM - drive back to Lahaina
• 11:30 PM - check into hostel at Lahaina

Thoughts

• This was an overall good use of a day. The drive up to Lahaina in the morning to go ride a jetski or do the chocolate tour wasn’t originally planned, but I’m glad I was able to find a few hours to do that.
• Jet ski was fun, but make sure to plan for some buffer time. The slots are 45 minutes, but that doesn’t include travel time. They try to give you 45 minutes on the jetski itself, but taking into account ~5-10 mins travel time on either side to the floating dock, plus waiting around, etc, I ended up having to cut my session a little early (~10 mins early), and I still only made it back at about 10:45 AM. I just barely was able to make it to the chocolate tour at 11:00 AM, which was about 10 min drive way.
• I think getting the pictures taken at jetski ($50 for me, supposedly 75 normally?) was worth it, but be sure to check your spam folder.
• Many guides will recommend going up to Haleakala to see the sunrise. I suppose you could do this, but you’d have to wake up at ~2 AM in order to have enough time to drive to the summit, which I didn’t particularly want to do on vacation. I thought the sunset was pretty enough, and it gave me some time to try to get some astrophotography shots at the end.
• Waiting until ~10PM to leave also meant that the road down the mountain was nearly completely empty, so it made for a very pleasant driving nighttime driving experience. Lots of twists and turns :).
• Make sure to bring warm winter clothing. It gets down to near freezing (40F or so) at the summit, if not colder.
• I got a little unlucky with the weather at the top of the mountain - when I arrived at ~5pm, it was very cloudy, and drizzling a little bit. I ended up taking a nap in my car instead of doing the hike I had originally planned. Luckily, it cleared up right before the sunset!
• Haleakala is a US national park, and can benefit from your national parks pass if you have one. Otherwise, entry was $30. I think you get a 2 day pass for 30, but it didn’t last me until my drive to Hana where I could enter the park from the other side :(. The park pass is only 65 or so, so it’s probably worth buying if you’re the outdoorsy type.

Day 3: Tuesday 5/30 - Scuba Day 1

• 8:00 AM - 5:30 PM - Scuba lessons at Maui Diving with Will
• Dinner at Earth Aloha Eats
• Rest and recover

Thoughts

• Scuba was very interesting, would recommend. Mostly.
• I ended up doing the e-learning on the Friday night + Saturday before I left (Sunday). I think it took ~10 hours total, which wasn’t too bad. I attempted to do it fairly thoroughly and didn’t feel like I missed much in that time.
• It would’ve helped if I had spent more time in / around the ocean growing up, as the first chunk of time we spent in the ocean was a little rough, especially the 200m swim requirement with no goggles.
• 2 students (out of 5) ended up being dropped from the class a little bit into the first dive, where the girl from the couple was having trouble getting under the water. She seemed to panic under the water and spit her regulator out of her mouth, which is a big no-no. The instructor spent some time with her trying to get her comfortable, but she didn’t seem to be getting it, so the instructor told her to try again later, and recommended a more 1:1 set of classes instead of the accelerated (2 days instead of 3) group (5 students) setting we were in.
• Learning to only breathe through your mouth instead of your nose is a strange feeling, especially when you typically do the opposite.
• I had some trouble keeping my mask empty throughout the dive, but I guess that gave me lots of practice for mask clearing skills. Apparently, this is just a thing people with moustaches have to live with. I’m not committed enough to scuba to shave just yet.
• I also had some trouble equalizing - I’m not sure if I just never quite got the technique figured out, or if it’s just something that becomes easier with practice, but I had more pressure in my ears than I would have liked. The other equalizations (lungs, mask) were fine, as the lungs were handled by the scuba regulator, and the mask was handled by just breathing out through my nose occasionally, which I was doing plenty of to clear my mask.
• I ended up not eating anything until the evening, except for one of those RXBAR bars. This was probably the right call for me, to minimize the chance of sea sickness / vomiting. Scuba isn’t very physically demanding once you’re actually in the water, and I didn’t really feel tired due to the lack of food. The other students and Will did a decent bit of snacking in between the two dives though, and they were both fine, so YMMV.
• I first stopped by Foodland to try and get some poke, which is apparently quite good, especially for grocery store food, but unfortunately they had closed by the time I got there. I did find some special Hawaiian bananas when I was there though, which was cool. Definitely worth trying, it’s apparently what makes the banana bread so good.
• The food truck had some fantastic vegan meat substitutes. Would recommend.

Day 4: Wednesday 5/31 - Scuba Day 2

• Check out of hostel
• 8:00 AM - 4:30 PM - Scuba lessons at Maui Diving with Will
• Dinner at Moku Roots
• Drive Nakalele blowhole, stop for some pictures and enjoy the coast
• Continue drive over to Kahului (via northwest side) and check into hotel

Thoughts

• The second day was better than the first.
• I generally felt more comfortable in the water, and I think we spent more time doing fun diving and swimming around. Apparently, we had done a lot of the harder stuff on the first day.
• There were a couple of specific skills that we did which I wasn’t particularly fond of, but Will specifically said that it’s better to not tell new divers which these were so they’re not going to scare themselves out of it, so I won’t. They were definitely a little uncomfortable, but I got through it, and it’s definitely not worth missing out on scuba because of it.
• My equalization troubles continued on the second day, and maybe even got a little worse? I think it was because we did a lot more descents / ascents, so there were more opportunities to get the equalization wrong. It’s definitely something I’ll need to practice a little more slowly whenever I try to go scuba diving next.
• I’ve had a bit of crackling in my ear (similar to what you get on a plane) for the past ~3 weeks after the second day of scuba, but it’s been getting better, and has mostly gone away now. I thin this is, again, related to the poor equalization. My doctor has recommended daily 4 hour sudafed + flonase to help clear up my sinuses / open up my ears. This might be helping, or the problem might just be getting better on its own?
• I had paid for the premium scuba package, which included “peak performance buoyancy” and nitrox certification. We didn’t end up doing the peak performance buoyancy while we were out in the water, and I had forgotten to ask about it. Luckily, it seems that’s not a specific certification on its own.
• We also forgot about the nitrox certification, but I asked Will about it at the very end of the day, and we got through it in about 30 minutes at the dive shop, as it just involved making sure that the tank was what it said. The nitrox e-learning was only about 2 hours.
• In hindsight, I probably should’ve just gone for the base package, and saved myself the extra $100 or so for the premium class and 200 for the nitrox e-learning. I think it’s unlikely that I’ll use nitrox immediately. I suppose it’s nice to have it and just be done with it, though?
• The restaurant was a recommendation from Will, and while it was decent, I thought it wasn’t as good as the food truck from yesterday. Apparently his wife really likes it, though. My guess is that Hawaii just isn’t big on vegetarian / vegan food, given how much fish there is around.
• The drive across the northwestern side of the island was beautiful. There was basically no one on the road - I think I saw maybe 10 cars for the entire ~1.5 hour drive. It was a lovely drive through the mountains, with lots of twists and turns, and the empty roads meant you could go pretty fast, at least around the sections you could see. There were some sections that were 1 car only, along the ~10 miles of not-state-highway in the middle, but as long as you’re paying attention to opposing cars and yielding at the right time, you should be fine.

Day 5: Thursday 6/1 - Road To Hana

• 12:30 PM - 7:00 PM - drive the road to Hana, and back

Thoughts

• This was not the best use of a day.
• I woke up a little late today, and didn’t end up getting out of bed until noon or so. This was explicitly not what the online guides recommended. Most guides will recommend hitting the road around 8 AM or so.
• I used the Shaka guide app to guide me through the tour. The app itself was fine, and actually had some interesting stories, but annoyingly, it kept pausing my music playing through Youtube Music when narrating (which was fine), but then didn’t resume it afterwards. Instead, I kept getting the music from the app itself. If you’re looking for a survey of hawaiian music, I suppose that works, but I wasn’t a fan of all of the music, and got annoyed when it nuked my choices …
• There were a ton of cars on the road, many of whom would drive at or under the speed limit. Sometimes people would be kind and pull over to let you pass them, but not everyone did this, or otherwise they took a long time. It made the drive very frustrating.
• There were a lot of stops recommended along the road to e.g. stop for a hike, get food, etc, but there wasn’t that much parking, so many of the stopping points I ended up skipping. I also didn’t have that much sunlight available, so I was trying to pick the stuff that looked the most interesting.
• When I got to Aunt Sandy’s place for banana bread, they were sold out. This was by maybe 2 or 3 pm. I was able to find some other banana bread at a shop a little further down, but it’s not the one that gets recommended everywhere on Reddit. Worth noting that this place is within Ke’Anae, a very slight detour from the main road to Hana. Taking the short detour was worth it regardless though, there’s a nice coast you get to see. Detour is like 2-3 mins.
• Many places along the road only (or preferably) take cash, so make sure you have some. The road to hana was the only place where I could’ve ended up needing cash, but it wasn’t strictly necessary.
• I unfortunately missed my reservation at the black sand beach - it was originally scheduled for Wednesday at 10 AM - 12:30 PM, but as I had to move my drive back a day due to scuba lessons getting rescheduled, I wasn’t able to get in. I did try to book a new reservation a week in advance (as opposed to 2 weeks for the first reservation), but nothing was available. If you’re going to go, try to book a month in advance in order to get the more desirable 12:30 - 2 PM slot, and consider booking multiple.
• Just about all the dinner options in Hana close by about 5:00 PM, so make sure you either pack some food, or snack along the way, or just are prepared to not eat.
• There’s a couple of neat fruit stands past Hana. I stopped at this one and had a cherimoya, which was kind of cool. Apparently the seeds will probably make you sick, and the skin is very bad for you, but the fruit itself was decent. I turned around after I got here.
• The “back side” (southeast) of the road was supposedly closed, according to the shaka guide, and is apparently generally a bad idea to drive. Most people will just turn around and drive right back the way they came on the road to hana. I had an AWD drive car and an emergency radio I borrowed from a friend, and was planning on driving the back road (assuming it was open), but ended up deciding against it given the time. Also, it’s potentially banned in some rental contracts, though at a glance I didn’t see anything about it in my rental from Sixt.
• If I was going to do it again, I’d definitely depart by ~8:00 AM, and then do one of the following options:
  • Drive all the way to Hana without taking any stops, and then start hitting things on my way back. Both roads should be more clear this way.
  • Take my time stopping on the way to Hana, and then drive on the back side when going back. This also gives you time to make it to the other side of Haleakala national park.
• Overall, though, I think I got the scenic driving views that the Road to Hana mostly offers on the drive from Lahaina to Kahului on the previous day, and probably should’ve found something else to do on this day.

Day 6: Friday 6/2 - Departure

• Chill in hotel until departure
• 2:58 PM - depart OGG to SFO

Thoughts

• I didn’t have any specific plans for the day, and had a 3 PM flight, so I ended up spending most of the morning in the hotel
• I tried to get last minute surfing lessons, but unfortunately when I had the idea the previous night, the place had already closed, and they weren’t able to get anyone at 8 - 10 AM. Next time, I’ll plan ahead :).

Overall Thoughts

• I took this trip mostly on a whim, with very little planning ahead of time. There was some natural downtime at work after Symposium, and I had a bunch of PTO to use, but wasn’t sure exactly how to use it. I’d always heard Hawaii was nice, so I booked a flight, but didn’t end up having much time to plan stuff given the rush up to Symposium.
• The trip was definitely worth it, but it would’ve been made better with a little more planning (e.g. for classes, restaurant reservations, etc).
• The most expensive part of the trip was the lodging - $200 a night minimum for a single room, typically closer to 250. There were a couple places that had shared room hostels for 90 a night or so, but I didn’t end up reserving any of those. Hawaii is definitely cheaper if you’re able to split the cost of lodging with someone you trust.

Old Notes From Workplace

An early, short version of this post that I posted to Workplace when someone at Meta asked for thoughts on Maui:

I just came back from a 5 night, 6 day trip to Maui. I stayed in a few different spots around the island. Some thoughts:

• IMO, Lahaina is the place to be. It seems to have the most active set of things to do near the beaches, and has what I thought was a great selection of food.
• There’s a ton of food trucks on Maui, I’d recommend getting > 50% of your meals from one .
• I stayed the first night in Kihei, but honestly apart from a couple of beaches (including Sunset Beach), I didn’t think there was much to do there. If I were to do it again, I’d have spent an extra night in Lahaina and just skipped Kihei altogether.
• I drove the Road to Hana, starting at ~noon (which is admittedly about 3-4 hours late) using the Shaka Guide app. The app was nice, but honestly I thought the drive was overrated. I wish I had spent my time doing something else. If you’re a little more adventurous, I’d instead recommend taking the road around the northwest side of Maui from Lahaina to Kahului. The scenery and roads are quite similar, but there’s significantly fewer drivers. I saw maybe ~10 people on the entire 1.5 hour drive, versus being stuck behind incredibly slow drivers for most of the duration of the Road To Hana.
• I enjoyed riding a jet ski, I hadn’t done that in ages and thought it was a blast. Would recommend. Be warned though, your forearms will be very sore for a while. I booked an hour (including travel time) which was ~45 minutes jet ski, but I gave up after ~30 mins because I felt like I couldn’t hold on anymore lol. I was running the thing at max the entire time though. If you’re riding with a second person, rather than going solo, filling the full 45 mins shouldn’t be a problem.
• I spent 2 days getting certified as a SCUBA diver with Maui Diving. I really enjoyed the experience and would highly recommend it if you’ve thought it’s something that’d interest you. Imo it was fairly approachable, though you should definitely be comfortable with the ocean and e.g. know how to swim (there’s a 200m swim test + 10 min water tread test at the very beginning). My instructor was Will, he was fantastic.
• I also really enjoyed driving up to the summit of Haleakala, and watching the sunset. Apparently the sunrise there was also nice, but honestly I cba waking up at 3am and driving 2 hours to catch it. I waited until everyone left after the sunset and then did some astrophotography, and then got to drive down the entire mountain at ~10pm in the dark with no one else there. Also a fantastic drive, would recommend . Ideally, get an AWD drive car for all the twists and turns, if you want to drive at substantially higher than the speed limit lmao.
• I enjoyed the Maui Chocolate Tour. A bit pricey, but it was a relaxing hour and a half after jet skiing, and I got to try out a bunch of unique chocolate flavors. Would recommend if you have a little cash to burn and time to kill.